Reactions of α-Hydroxy Carbonyl Compounds with Azodicarboxylates and Triphenylphosphine: Synthesis of α-N-Hydroxy Amino Acid Derivatives

Article abstract of DOI:10.1021/jo00231a026

Reaction of aliphatic α-hydroxy esters with azodicarboxylates and triphenylphosphine in the presence of either CbzNHOCH2Ph or trOCNHOCH2Ph provides a direct route to protected α-N-hydroxy amino acids.Similar reactions with aromatic α-hydroxy carbonyl compounds and derivatives result in predominate oxidation to the corresponding α-oxo carbonyl derivatives.